Herbicidal poly uracils



nited States Patent Int. Cl. A01n 9/22; C07d /30 US. Cl. 260-260 ClaimsABSTRACT OF THE DISCLOSURE The poly uracils of the formula below areuseful as herbicides:

where the compounds may be symmetrical or unsymmetrical and R is alkylof 3 to 8 carbons, phenyl, benzyl, cycloalkyl of 5 to 8 carbons, orcycloalkyl of 5 to 8 carbons substituted with methyl or methoxy; R isalkyl of 1 to 3 carbons; X is methyl, chlorine, bromine and iodine andcan be hydrogen when R is cycloalkyl, with the proviso that X and R canform a trimethylene or tetramethylene bridge; and Z is Where R ishydrogen or alkyl of l to 4 carbons and R is alkylene of 1 to 12carbons, alkenylene of 1 to 12 carbons, cyclohexylene, and phenylene.

CROSS REFERENCE TO RELATED APPLICATIONS This application is a divisionalof my co-pending application Ser. No. 744,309 filed July 12, 1968 nowUS. Pat. No. 3,471,282, which in turn is a continuation-in-part of mythen co-pending application Ser. No. 622,469, filed Mar. 13, 1967, nowabandoned which application is a continuation-in-part application of mythen co-pending application Ser. No. 539,673, filed Apr. 4, 1966, nowabandoned.

BRIEF SUMMARY OF THE INVENTION This invention relates to novelcompounds, which for the sake of simplicity can be called poly uracils,and their use in herbicidal compositions.

The compounds are represented by the following structural formula:

ice

wherein:

R can be the same or different at the two positions indicated and isselected from the group consisting of alkyl of 3 to 8 carbon atoms,phenyl, benzyl, cycloalkyl of 5 to 8 carbon atoms and substitutedcycloalkyl of 5 to 8 carbon atoms wherein said substituent(s) isselected from the group consisting of methyl and methoxy;

R can be the same or different at the two positions indicated and isselected from alkyl of 1 to 3 carbon atoms;

X can be the same or different at the two positions indicated and isselected from the group consisting of methyl, chlorine, bromine, andiodine; and can be hydrogen provided the R on the same ring iscycloalkyl, and with the further proviso that X can be joined with R toform a trimethylene or tetramethylene bridge; and

Z is selected from the group consisting of where R is hydrogen or alkylof 1 to 4 carbon atoms and R is a divalent radical selected fromalkylene of 1 through 12 carbon atoms, alkenylene of 1 through 12 carbonatoms, cyclohexylene and phenylene.

Preferred compounds Within the above formula are those where R, R and Xare the same as above, however the compound is symmetrical and Z isExemplary of the preferred compounds are the following:

1,1'-oXalyl bis (3-sec.-butyl-5-bromo-6-methyluracil) 1,1'-oxalyl bis(3-iso.-propyl-5-bromo-6-methy1uracil) 1,1'oxalyl bis(3-iso.-propyl-5-chloro-6-methyluracil) 1,1-oxalyl bis(3-tert.-butyl-5-chloro-6-methyluracil) 1,1'-oXalyl bis[(3-cyclohexyl-6,7-dihydro-S-cyclopenta (d)pyrimidine-2,4-(1H,3H)-dione] 1,l-oXalyl bis (3-tert.-butyl-5-bromo-6-methy1uracil) Thereis the possibility that the Z-linkage occurs through the 2-positionedoxygens rather than through the l-positioned nitrogens as shown in theformula above since uracils may react in their enol or keto form as:

Absorption spectral evidence (infra-red) for the Z- oxygen linkage isstrongly suggested by the products of this invention where Z is derivedfrom phosgene Thus both products (Z-nitrogen or Z-oxygen linkage) ormixtures of these linkages are considered within the scope of thisinvention. For the sake of clarity or brevity however, the compoundswill be named assuming the reaction to have occurred on the l-nitrogen.

The above compounds are useful in herbicidal compositions. Thesecompositions are mainly useful as soil sterilants but are also useful asselective herbicidal agents in certain crops.

3 DETAILED DESCRIPTION OF THE INVENTION ,The compounds can be preparedby treating two equivalents of the sodio derivative of an appropriatelysubstituted uracil with one equivalent of a bifunctional acid chlorideas illustrated by the following reaction (4):

where R, R X and Z are as defined above.

Alternatively, these compounds can be prepared by the reaction of a1-(w-halooxygenatedhydrocarbo)uracil with the sodio derivative of asecond uracil, in which R, R and X are not necessarily the same for thetwo uracil rings coupled together. This reaction (5) is illustrated bythe following equations:

Step 1 I o R Cit lents of the sodio derivatives of a uracil and oneequivalent of a bifunctional acid chloride is stirred from 2 to 24 hoursat temperatures from 20 to C. The product can be isolated in any ofseveral ways, such as (1) filtration, followed by a water wash to removeinorganics leaving behind essentially pure product; (2) vacuum strippingof the solvent, followed by treatment with base to remove uncoupleduracil, filtration and water wash as above. Purification, if necessary,is accomplished by recrystallization from common organic solvents or bychemical extraction.

The first step of reaction (5) is performed in the presence of any ofseveral inert solvents, such as tetrahydrofuran, dioxane,dimethylformamide, chloroform or benzene to facilitate mixing of thereactants. The mixture of bifunctional acid chloride, one equivalent ofa sodio derivative of an appropriately substituted uracil is stirred for/2 to 24 hours at temperatures of from 0 to 75 C. To the above stirredmixture of l-(w-halooxygenatedhydrocarbo)uracil is added a secondequivalent of an ap-. propriately substituted uracil.

It has been noted, however, that when the bifunctional acid chloride isoxalyl chloride, the yield of polyuracil may be increased when a 1:1mole ratio of oxalyl chloride to uracil is employed rather than the 1:2mole ratio of bifunctional acid chloride to uracil as is taughthereinbefore.

The second step of reaction (5) involves stirring for from 2 to 24 hoursat temperatures of from 20 to 75 C. Product isolation can be performedas described for reaction (4).

In order to more fully describe this invention the following additionalexamples are given. All parts are parts by weight unless otherwiseindicated.

EXAMPLE 1 1,1'-carbonyl bis(5-bromo-3-sec-butyl-6-methyluracil) A totalof 28 parts of 5-bromo-3-sec-butyl-6-methylnracil sodio derivative issuspended in 200 parts of tetrahydrofuran. Slowly with stirring 5 partsof phosgene are added. The temperature is allowed to riseautogenetically, then the reaction is stirred at room temperature for 16hours. The solvent is removed under reduced pressure and the residuetreated at 0 with 4 parts of sodium hydroxide contained in parts ofwater. The solid is filtered, washed with water and dried and isessentially pure 1,1- carbonyl bis(5-bromo-3-sec-butyl-6-methyluracil),M.P. 220.

EXAMPLE 2 l,l'-oxalyl bis (3-tert.-butyl-5-chloro-6-methyluracil) Twohundred parts of anhydrous tetrahydrofuran is placed in a 3-neck flaskequipped with a stirrer, condenser and an addition funnel. Four and twotenths parts of a 60% suspension of sodium hydride (in mineral oil) ischarged into the stirring flask followed by 21.6 parts of 3 tert. butylS-chloro-6-methyluracil. This mixture is stirred at ambient temperaturefor 16 hours.

Oxalyl chloride, 6.3 parts is added drop-wise to the above vigorouslystirred mixture. Stirring is continued for an additional four hours,then the reaction mixture is poured into 2000 parts of cold 2% aqueoussodium hydroxide solution. The precipitated solids collected byfiltration, washed with water then recrystallized from ethanol gaveessentially pure 1,1'-oxalyl bis(3-tert.-butyl-5-chloro-6-methyluracil), M.P. l72172.5 C.

EXAMPLE 3 The following products can be prepared by substituting theappropriate amounts of the following uracil sodio derivatives andpolyfunctional acid chlorides for S-bromo- 3-sec-butyl-6-methyluracilsodium salt and phosgene cited in Example 1 or the3-tert.-butyl-5-chloro-6-methyluracil sodium salt and oxalyl chloride ofExample 2.

Substituted uracil sodio derivatives Polyfunctional acid chloride I1,l-oxohydrocarb0bis(substituted uracil)3-sec-butyl-5-bromo-6-methyluracilsodio salt Oxalyl chloride1,1-o)g13i1bis({i-scc-butyl-fi-bromo-G- I118 y urac Do. Malonyldichloride 1,1-malonylbis(3-sec-buty1-5-bromo-6- methyluracil Do.Succinyl dichloride 1,1-succinylbis(3-sec-buty1-5-brom0-6- methyluracil)D0 Adipoyl dichloride 1,1-adip0ylbis(3-sec-butyl-fi-bromo-G-methyluracil) Do Scbacyl dichloride 1,1-scbacylbis(3-scc-buty1-5-brom0-6methyluracil). Do Phthalyl dichloride1,1-phthalylbis(3-scc-butyl-5-br0m0-6- mcthyluracil) D0- Isophthalyldichloride. 1,1-isophthalylbis(3 scc-buty1-5-br .6.

methyluracil) Do T phthalyl dichloride1,1-tcrcphthalylbis(3-sec-buty1-5-br .6.

methyluracil) Do Pcrhydrophthalyl dichloride1,l-pcrhydrophthaly1bis(3-sec-butyl-5-bro o G-methyluracil) DPcrhydroisophthalyl dichloride1,1'-pc1hydroisophthalylbis(3-seo-buty1-5- bromc-d-rnethyluracil DPcrhydrotcrcphthalyl dichloride1,1'-perhydrotercphthalylbis(3-sec-buty1-5- bromo-G-mcthylurac' DoFumaryl chloride 1,1-Iu1 narylbis (3-sec buty1-5-b10mo-6-methy1- urac 3..1 uty1-5 chloro-fi-methyluracil sodio salt Oxalyl chloride 1,omglbis(3-soc-bu yl-fi-chloro-fi-methyluraci3-tert-butyl-5-chloro-6-cthylu.racil sodio salt ..do 1,1-OXa1ly1biS(3-tert-buty1-5chlor0-6-ethyl- 1118013-(iso-propy1)-5-bromo-6-methyh1tacil sodio salt ..d01,1-0g13i1bi$[-(3-iS0-pr0py1)5-bron10-6- me y urac3-secbutyl5-chl0r0-6-ethylura0i1SOdiO salt .d01,l-0Xaly1biS(3-Sec-butyl-5-ch10r0-6-cthyluracil) 3-tert-butyl-5-bromo-6n-propylm'acil sodio salt Phosgene 1,1-carbfm 1t%s(a-t rt b t 1.5.

propy uracl 3-iso-propyl-5-iodc-6-iso-propyluracil sodio salt Malonyldichloride 1,1-ma1i)ny1t li) 3-is0-p1opyI-5.j d .6 j

propy uraci 3 (3. eni;y1)-5-br mo-6-methy1u1acilsodio salt Oxalylchloride- -0Xalall isw-(ti-pe tyl)-5- romo-6-methyl- 'lll'aCl3-n-butyl-5,fi-dimcthyluracil sodio salt Fumaryl chloride1,1-iumarylbis(3n-butyl-5,G-dimethyluracil).3-(n-hcxyl-fi-chloro-Bcthyluracil sodio sa1t Phthalyl dichlorid1,1-phtha1ylbis(3-n-hcxyl-fi-chloro-(i-ethyluracil). Fmnaryl chloridel,ldmiriarylbis(B-tert-octyl-S-iodo-fi-ethylurac3-n-propy1-5-methyl-G-ethyluracil sodio salt 1,2,3,6 tetrahydrophthalyldichloride.... l,12 -1,2,gait-tegrathydrophgialylbis (3-11-pr0py1- -me y'6 1y 1112101 3- 3- entyl -5chl0ro-6mcthyll1.raci1sOdiO salt Oxalylchloride 1,1-0Xa1y1biS[3-(3-pelltyl)-5-ch1oro-6-methylura- 1 oil] 3-ec-butyl-5-iodo-6-methyluracilsodio salt Succinyl dichloride1,1sucfiinrllbis(3-5ec-butyl-5-i0d0-dmethy1- uraci3-phcny15bromo-6-methyluraci1sodio salt Phosgene 1,1-car l)onylbis(3-phenyl-5-bromo-6-methyluraci3-benzy1-5-bromofi-mctllyluracilsodio salt Itaconyl dichloride 1,1-itacinylbis(3-benzyl-5-bromo-6m1ethyl- 1113013-pl1cnyl-5-chl0ro-6-etl1yluraci1 sodio salt Sebacyl dichloride1,1-scbacy1bis(3-phenyl-5-chloro-6-ethyluraci1)3-cyclopcnty1-5-chloro-fi-methyluracilsodio salt Glutaconyl dichloride1,1 glgtaconylbis(3-cyc1opentyl-5-eh1 -6- me y urac 3cyclohexyl-5-bromo-6methyh1raci1sodio salt Phosgene l,l-carlii)onylbis(3-cyclohexyl-5-bromo-6-methyl uraci3-cyclohcpty1'5-brorn0-6-methyluracilsodio salt Pcrhydroterephthalyldichloride 1,l-perhylrotife ihthalglbisG-eycloheptylromo- -me 1y uraei3-cyclooctyl-5-methyl-dn-propyluracil sodio salt Succinyl dichloride 1,1-sl1c iinyll )1is(3-cyclooctyl-EmethyLG-npropy uraci3(2-methylcyclohexyl)-5brom0-6-etl1y1uracilsodio salt Phosgene 1,g-carbolygois w-(Z-rfiethylcyclohexyl)-5- romo- -e 1y uracl 3-2-methoxycyclohexy1)-5-icdo-6-methyluracilsodio salt.... Oxalyl chloride1,1-oxalylbis [3-(2-methoxycyclohexyl)-5- iodo-fi-methyluracil]3-cyclohexyl-G-methyluracilsodio salt Phosgcne1,1-carbonylbis(3-cyclolicxyl-fi-methyluracil)3-cyclooctyl-fi-ethyluracilsodio salt Oxalyl chloride...1,1-oxalylbis(B-cyclooctyl-(i-ethyluracil). 3-cyc10pcntyl6cthyluracilsodio salt Malonyl dichloride. 1,1-rnaloylbis(3;cyclopentyl-fi-ethyluracil). 3-(2methylcyclohcxyl)dimethyluracilsodio salt Isophthalyl dichloride1,g-isogththalyllfis[3-(2-methylcyclohexyb- -me yuraci3-(3metl1oxycyclohcxyl)-6-ethyluracilsodio salt Oxalyl chloride 1,l2)!alylbis?(3-mcthoxycyclohexy1)-6- e 1y uraci3sec-butyl-5-methyl-6-isopropyurlacilsodio salt Succinyl dichloride1,1-succnylbis3-sec-butyl-5-methy1&iso-

propy 1111101 3(Z-methylcyglohexyl-5,6,a,8 tetrahydro-2,4-(1H,3H)-Phosgene 1,gfir gni lbigi&? lrln%i3lig lcycloheiryl)5,6,7,

quinazoline ione so io sa t e ra y 'q i118 o el-3-cyclol1exyl-6,7-dihydro5-cyclopcnta[d] pyrimidine-2,4- .-...do1,1-carbonylbis[3-oyclohexyl-6,7-dihydr0-5- one3-tert-butyl-5,6,7,8-tetraliydro-2,4-[1H,3H]-quinazolinediono Oxalylchloride 1,g-flgglggg -tert-buiiylfi6,7,8itetrahydrosodio salt. uinazoine ione. 3-iso-propyl-Ea,6,7,8-tetrahydro 2,4-[1H,3H1-quina2olin6dioneMalonyl dichloride l,l lrl(t l ong l?)is 3- iso-pr opg-5,6,il,8-tetrahydrosodio salt. qu1nazo ine ione 3pheny1-5,6,7,S-tctrahydro-ZA-[1H,3H1-quinazolinedione Phthalyldichloride 1,gglhf l agggnis[3;pheriyl-fifi,7,8itetrahydrosodio salt.-qmnaz0i11e ione3-5ec-butyl-5,6,7,8-tctrahydlo-2A-[1H,3H]-quinazolinedione Phosgene1,1-carbonylbis[3-scc-butyl-5,6,7,8-tetrahydrosodio salt2,441H,3H)quinazolinedione].

3-cyclcoctyl-5,6,7,8tetrahydro-2,4-[1H,3H]-quinazo1inedione Adipoyldichloride sodio salt.

3-scc-butyl-G,7-dihydro-5-cyclopenta[d]pyrimidine-2,4'UH, Oxalylchloride SHI-dione sodio salt.

3-iso-propyl-(i,7-dihydro-5-cycl0penta[d]pyrimidine-2,4-[1H, Citraconyldichloride 1,1cit1'aconylbis[3-iso-propy1-6,7-dihydr -5- 3H]-dione sodiosalt. gyclorfentaw)pyrimidine-2,4-(1H,3H)-

ione 3-cyclohexyl-6,7dihydro-5-cyclopenta[d]pyrimidine-2,4- Oxalylchloride 1,1-oxalylbis[3 cyclohexyl-6,7 dihydro-5- [1H,3H1-dione sodiosalt. cyclopenta(d)pyrimidine-2,4-(1H,3H)-dione].3-(pcntyl)6-,7-dihydro-5-cyclopenta[d]pyrimidine-2,4- Phosgene1,1-carbonylbis[3-(3-pentyl)-6,7-dihydro-5- [1H,3H1-clionc sodio salt.cyclopenta(d)pyrimidine-2,4-(1H,3H)-dione].3-sec-butyl-5-iodo-6-methyluracil sodio salt ..do1,1-carbo11ylbis(3-sec-butyl-5-iod0-6- methyluracil) 3tert-butyl-5-chloro-fi-mcthyluracil sodio salt ..dol,l-carbonylbis(3-tert-butyts-ehloro-fimethyluracil)3-tert-butyl-5-bromc-6methyluracil sodio salt Oxalyl chloride.1,1'-0)g13i1bl$(3-tert-buty1-5-br0m0-fime y mac 3-(2-1)entyl)5-bromo-6-methyluracil sodio salt. do-1,1-oxalylbis[3-(2-pentyD-5-brom06- methyluracil].3-sec-buty1-5chloro-6-cthyluracil sodio salt Phosgene 1,1 1:1ar1bonyl1l;is(3-sec-butyl-5-chl0r0-6- e y uraci3-tert-butyl-5-bromo-6-n-propyluracil sodio salt Malonyl dichloride 1,1ma10n 1bis(g-t rt-b 1.

propyluracil).

Substituted uracil sodio derivatives Polyiunctional acid chloride1,1-xohydrocarbobis (substituted uracil) 3-iSo-propyl-5i0d06isopropyluracial sodio salt Oxalyl chloride-1,10xalir1bis3is0-propyl5iodo-ti-isopropy urac3-(3-pe11tyl)-5-bromo-6-n1ethyluracil sodio salt Phosgcuc1,1-carb0nylbis[3- (3-pcutyl)-5-bron1o-6- mcthyluracil]. 1,1-glutarylbis(3-n-butyl-516-dimcthyluracil).

3-n-butyl-5, G-dimethyluracil sodio salt Glutaryl dichloride.B-(n-hexyl)--cl1loro-(i-ethyluracil sodio salt Suberyl dichloride 1,lt-sulicryllgs(3-n-hexyl-5-ehl0ro-6- e hy uraci3-tcrt-octyl)-5iodo-6-etl1yluracil sodio salt Azelayl dichloride 1,1-azelaylbis(3-tert-octyl-s-iodo-oethyluraeil)3-n-pr0pyl-5-incthyl-fi-ethylurucil sodio salt. Iiuielyl dichloride l,lt-tpirlnelyllgs(3-n-propyl-5-1ncthyl-tie y uraci3-tert-butyl-5-chloro-6-ethyluracil sodio salt Ihosgeue 1,1-carbouylbis(3-tert-butyl-5-chloro-6- ethyluracil).3-(3-pentyl)-5-ehloro-6-methyluracil sodio salt .do 1,1-carb0uy1bis[3-(3-pentyl)-Erch1oro-6- methyluracil].3-sec-butyl-5-i0do-fi-methyluracil sodio salt "do l,1-carbouylbis(3-sec-butyl-5-iodo-6- methyluracil)3-phenyl-5-brorno-6-methyluracil sodio salt do 1,1-carb0nylbis(3-phcnyl-5-bromo-d methyluracil)3-benzyl-5-bromo-6-methyluraeil sodio salt Oxalyl chloride 1,1-oxalylbis(3-benzyl-5-bromo-6- methyluracil)3-phenyl-5-chloro-S-ethyluracil sodio salt do 1, 1-oxalylbis(3phenyl-5-chl0r0-6- ethyluracil). 3-cyclopentyl-5-ehloro-6-rnethyluracilsodio salt .do 1,1-oxalylbis(3-cyclopentyl-5-chloro-6- methyluracil).3-cyclohexyl-5-bromo-6-methyluracil sodio salt .do 1,lmgylbis(3-cycloheXyl-5-bromo-6-methy1- uraci3-cyc1oheptyl-dbromo-Sqnethyluracil sodio salt Phosgene1,1-earbonyllois(3-cycloheptyl-5-brom0-6- brom o-fi-methyluraeil)3-cyclooctyl-5-methyl-6n-propyluraeil sodio salt .do 1,1-carl%cnyl li;s(3 eyclooctyl-5methyl-6npropy uraci3-(Z-methylcyclohexyl)-5-brorno-6-ethyluracil sodio salt Oxalylchloride- 1,laixzilylhisP-(2-methylcyclohexyl)-5-bromee w uraci3-(2-methoxycyclohexyl)-5-iodo-6-methyluracil sodio salt- Phosgeue1,1-carbonylbis[3-(2-methoxycyolohexyl)-5- iodo-ti-methyluracil].3-(3-methylcyclohexyl)-5-chloro-6-mcthyluracil sodio salt- Melony]dichloride 1,1-malenylbis[3-(3methylcyclohexyl)-5-chloro-6-methyluracil]. 3-cyclohexyl-fi-methyluracil sodio salt Pimelyldichloride 1,1-pimely1bis(Beyclohexyl-fi-rnethyluracil).3-cyclooctyl-G-ethyluracil sodio salt Succinyldichloride.1,1-succinylbis(3-cycl0octyl-G-ethyluracil). 3-cyclopentyHS-ethyluracilsodio salt Phthalyl dichloride.1,l-phtha1ybis(3-cyclopentyl-6-ethyluraeil).3-(2-methylcyclohexyl)-6-methyluracilsodio salt Phosgene l,lcarhonylbis[3-(2-methylcyclohexyl) 6- methyluracil]. 3(&methoxycyclohexyl)-6ethyluraeil sodio salt ..do1,1-carb0nylbis[3-(3-methoxycyclohexyl)- G-ethyluracil].3-sec-butyl-5methyl-fi-isopropyluracil sodio salt d01,1-carb{mylbis(3'sec-butyl-fi-methyl-fi-isopropy urac3-(2-methylcyclohcxyl)-5,6,7,S-tetrahydro-2,4-[1H,3H]- Oxalyl chloride-1,1-oxalylbis[3-(2-methylcyclohexyl)-5,6,7,8-

quinazolinedione sodio s t. tetrahydro-2A-(lH,3H)-quinazolinedione].3-cyclohexyl-6,7-dihydro-5-cycl0penta[d]pyrimidine-2,4- Sebacyldichloride 1,1-sebacylbis[3-cyelohexyl-6,7-dihydro-5- [1H,3H1-dionesodio salt. cyclopenta(d)pyrimidine-2,4-(1H,3H) dione],3-tertbutyl-5,6,7,8-tetrahydro-2,4-[1H,3H]-quinazolinedione3,3-dimetl1ylglutaryl dichloride1,1-(3,3-dimethylglutaryl)bis[3tert-butyldlone].1,1'-carbonylbisl3-iso-propy1-5,6,7,8teti-a11ydr SOdlO sal2,4-(1H,3H)-quinazolinedione].3-phenyl-5,6,7,8-tetrahydro-2,4-[1H,3H]-quinazolinedione d01,1-carbonylbis[3-phenyl-5,6,7,8-tetrahydrosodio salt. I2,4(1H,3H)-quinazolinedione].3-see-butyl-5,6,7,8-tetrahydro-2,4-[1H,3H1-quinazolinedi0ucIsophthaly1d1chlor1de 1,lisophthalylbis[3sec-butyl-5,6,7,8-tetrasodiosalt hydro-2,4-(1H,3H)-quinaz0linedione].

3-cyclooctyl-5,6,7,8-tetrahydro-2,4-[1H,3H]-quinazelinedione Oxalylchloride. 1,1-oxalylbis[3-cycl00ctyl-5,6,7,8-tetrahydro-2,4-(1H,3H)-quinazo1inedioue].

sodio salt. 3-iso-propyl-5,6,7,8-tetrahydro-2,4-[1H,3H]-quinazolinedionesodio salt. 3-scc-butyl-6,7-dihydro-5-cyc1openta[d]pyrimidineZA-Phosgene 1,1-carbonylbisl3-sec-butyl-6,7-clihydro-5- [1H,3H1-dione sodiosalt. cyclopenta(d)pyrimidine-2,4-(1H,3H)-dione].3-iso-propyl-6,7-dihydre-5-cyclopenta[d]pyrimidine-2,4-Perhydrctercphthalyldichlonde1,1-perhydroterephthalylbis[3isopropyl-6,7- [1H,3H1-dione sodio salt.dihydro-5-cyclopenta(d)pyrimidine-2,4-

(lH,3H)-dione]. 3-benzyl-6,7-dihydro-5cyclopenta[d]pyrimidine-2,4-Phosgene 1,1-carbonylbis[3-benzyl-6,7-dihydro-5-eyc1 [1H,3H1-dioue sodiosalt. penta(d)pyrimidine-2,4-(1H,3H)-dione].S-(S-pentyl)-6,7-dihydro-5-cyclopenta[d]pyrimidine-2,4- Phthalyldichloride 1,1-phthalylbis[3-(3-penty1)6-7-dihydm-5- [1H,3H1-dionesodios cyclopenta(d)pyrimidine-2,4-(1H,3H)di ne]3-5ec-butyl-5-iodo-G-methyluraeilsodio salt Oxalylchloridc1,1-oxa1l)ylbis(3-5ec-butyl-5-iodo-6-methy1- uraci3-tcrt-butyl-fi-chlorofi-methyluracil sodio salt ..do1,1-oxalylbis(3-tert-butyl-5-ch1oro-6-methylurac3-tert-butyl-ibromo-fi-methyluracilsodio salt Phosgene1,1'icarbolr)1y1bis(3-tert-buty1-5 b .6 th.

y uraci 3-(Z-pentyl)-5bromo-6-methyluraeilsodio salt Traumatyldichloride 1,1itrau fiaty1bi [3 (2- m; 1).5.

y uraci EXAMPLE 4 at C. The solvent is removed at reduced pressure and oa 5-br0=m0-3-sec-butyl-1-(5-br0m0-3-tert-butyl-1,2,3,4-tetra 2 31553222313? g gf sage r l it g hydiroxltde hydro-6-'methyl-2,4-dioxol-pyrimidinyl carb0nyl)-6- 1 r 1011 an Wa er methyluracil wash yieldsessentially pure S-brorno 3-sec-butyl-1-(5- brom0-3-tert-buty11,2,3,4-tetrahydro-6-methyl 2,4-di- A total of 14 parts of5-bromo-3-sec-butyl-6-methyl -py y carbonyl)-6-methyhlfaciluracil sodiumsalt is suspended in 200 parts of tetrahy- EXAMPLE 5 drofuran andstirred for a short time. Slowly, with stirring, is added 5 parts ofphosgene at temperatures between 10 and 0 C., the reaction mixture isthen allowed to stir at these temperatures for 24 hours. Slowly, withthe appropflate amounts of 1-(w-ha100Xyg6I1atedhYdf0- stirring, is thenadded 14 parts of 5-brorn0-3-tert-butyl-6- 3,5,64ri5l1bstituted)uracilfor the in situ g'snefated methyluracil sodium salt and the temperatureis allowed chlorocarbonyl-3-sec-butyl 5-bromo-6-methyluracil and to riseto a temperature not greater than usually 35 3-tert-butyl-5-bromo-6methyluracil sodium salt given in is maximum, This mixture is allowed tostir for 24 hours 75 Example 4.

The following products can be prepared by substitutingl-(w-halooxygenated-hydrocarbo)-3,5,G-trisubstituted uracil3,5,6-trisubstituted uracil, sodio derivatives Productl-ehlorocarbonyl-B-tert-butyl--bromo-6-methy1uracil3-tert-butyl-5-ehloro-6methyluracil sodio salt3-tert-butyl-5-ehloro-1-(5-br0mo-3- tert-butyl-l,2,3,4-tetrahydro-6-methyl-2,4-dioxo-1-pyrimidinyl carbonyl)-6-methyluracil.l-chlorooxalyl-Zi-see-butyl-5-bromo-6-methyluracil do3-tert-butyl-5-ehloro-1-(3-sec-butyl- 5-bromo-1,2,3,4-tetrahydro-6-methyl-2,4-dioxo-1-pyrimidinyl oxalyl)-6methyluracil.l-clilorocarbonyl-3-seebutyl-5-brom0-6methyluracil3-(Zqnethyleyelohexyl)-5,6,7,8-tetrahydro-2A-[1H,B-(Z-methylcyclohexyl)-1-(3-see- 3H1-quiuazolinedione sodio salt.butyl-E-bromo-LZ,3,4-tetrahydro- 6-metl1yl-2,4-dioxo-l-pyrimidinylcarbonyl)-5,6,7,8-tetrahydro-2,4- [1H,3H1-quinazolinedione.l-ehloromalonyl-3-tert-butyl-5-chloro-6-methyluraci13-(2-pentyl)-5-bromo-6-methyluracil sodio salt- 3-(2-pentyl)-5bromo-l-(3-tert-butyl- 5-ehloro-1,2,3,4-tetrahydro-6-methyl-2,4-dioxo-Lpyrimidinyl malonyl) 6-methyluraeil.1-chlerooxaly1-3-tert-buty1-ebromo-emethyluraeil3-sec-butyl-5-bromo-6-methyluraeilsodio salt3-see-butyl-5-bromo-1-(3-tert-butyl- 5 bromo-1,2,3,4-tetrahydr0-2,4-dioxo-l-pyrimidinyl oxalyD-fimethyluraeil.l-chloroearbony1-3-sec-butyl-5-chloro-G-methyluraeil 3-eycloheXy1--methvluracilsodio salt 3-cyclohexyl-I-(S-see-butyl-S-chloro-1,2,3,4-tetrahydro-2,4-dioxo-1- pyririiidinyl carbonyl) -6 n1ethyluraeil-ehlorocarbonyl-3-phenyl-eehloro-fi-methyluracil3-benzyl-5-br0m0-6-methyluraeilsodio salt.3-10enzyl-5-bromo-1-(3-pheny1-5- ehloro-l,2,BA-tetrahydr0-2,4diox0-l-pryimidinyl earbonyD-fimethyluraeil.

EXAMPLE 6 1,1-(1-oxoethylene) bis-[-3-cyclohexyl-6,7-dihydroll, ('loxoethylene) 5-cyclopenta (d) pyrim1dine-2,4-(1H,3H)-dione]methyluracil) The poly uracils of the invention can be admixed with TWOhundred parts of dry tetrahydrofuran is placed pest control adjuvants ormodifiers to provide herbicidal in a reactor equipped with an agitatorand a reflux concomposmonsl m tha form dusts, granules P denser. A 60%suspension of sodium hydride (in mineral water'dlspil'slbk) P g gth C hCntrateS, Oil), 2 parts is charged into the Stirring reactor f 1 andemuls1ons and solutions or dispersions in organic lowed by 24.7 parts of5-bromo-3-isopropyl-6-methylhquldsuracil. This mixture is stirred atambient temperature the P T210118 can be sed Wlth a carrier or for 16hours diluent agent such as a finely divided solid, an organicChloroacetyl chloride 5.6 parts is added gradually to hquld, a w gagent, a dispersing agent, or any suitthe above stirring mixture. Afterthe addition is comable combl,n atlon of F P- plete, the reactionmixture is stirred an additional 4 CPmPOSIHOHS Contalnlng the P y C lespecially hours then poured into 2000 parts of ice cold 2% aque liquidsand 'wettable powders, contain as a conditioning ous sodium hydroxidesolution. The precipitated solid agent one surface-3cm"? g m tlmeScollected by filtration, washed with water until alkali- 40 called PPamollnts sufilclent Q l er the f is technical grade 1,1' (1 OXOethy1ene)composition readily dispersible in water or in oil. Ibromo-3-isopropyl-6-methyluracil) which can be purii surface'actlve agent used fled by recrystallization from ethanoL persrng or anemulslfying agent which will assist dis- Equivalent amounts of thecorresponding reagents Perslon of the Compound e agent or (appropriate(it-halogenated acid chlorides and uracils) can lnclude Such 2111101110,catlonlc and noncan be substituted for the chloroacetyl chloride and 5-t agents as have herefcffore beef} generally employed bromoadso propyl 6methyluracil of the procedure in plant control compositions of similartype. S u1table above and the following compounds of this inventionsurface-active agents are set forth, for example, in can be prepared;tergents and Emulsifiers 1965 Annual by John W.

McCutcheon, Inc. 1,1-(1-oxoethylene) bis-(5-bromo-3-sec.-butyl-6 Ingeneral, less than 10% by weight of the surfacemethyluracil) activeagent Will be used and ordinarily the amount of1,1'-(1-oXo-2-methylethylene) bis-(5-bromo-3-sec.- surface-active agentswill range from 1-5% but may even butyl-6-methyluracil) be less than 1%by weight.

1,1'-(1-oxo-2-methylethylene) bis-(5-chloro-3-cyclo- Additionalsurface-active agents can be added to the hexyl-6-methyluracil) 5rformulations to increase the ratio of surfactant: poly1,1'-(1-oxoethylene) bis-[5-chloro-3-(1-ethylpropyl)- uracil up to ashigh as 5:1 by Weight. Such compositions 6-methyluracil] have a greaterherbicidal effectiveness than can be ex- 1,1-(1-oxo-2-methylethylene)bis-(5chloro-3-tert.- pected from a consideration of the activity of thecombutyl-6-methyluracil) ponents used separately. When used at higherrates it is 1,1-(1-oxoethylene) bis-(5-bromo'3-tert.butyl-6- 6Opreferred that the surfactant be present in the range of methyluracil)one-fifth to five parts surfactant for each one part of 1, 1-(l-oxoethylene) bis- (5-chloro-3-benzyl-6-methylpoly uracil.

uracil) Wettable powders are water-dispersible compositions1,1'-'(1-0xoethylene) bis-(5-bromo-3-phenyl-6-methylcontaining the polyuracil, an inert solid extender, and il) one or more surfactants toprovide rapid wetting and 1,1'-(1-ox0-2-butylethylene)bis-(5-chloro-3-isopropylprevent heavy flocculation when suspended inwater.

6-methyluracil) The classes of extenders suitable are the natural clays,1,1-(1-oxo-2-ethylethylene) bis-(5-bromo-3-isopropyldiato-maceousearths, and synthetic mineral fillers derived 6-methyluracil) fromsilica and silicates. Most preferred fillers are kaolin-1,1'-(1-oxo-2-methylethylene) bis-(5-iodo-3-isopropylites, attapulgiteclay, montmorillonite clays, synthetic 6-methyluracil) silicas,synthetic magnesium silicate and calcium sulfate 1,1'-(1-oxoethylene)bis- 3-cyclohexyl-6-methyluracil) dihydrate. 1,l-(1-oxoethylene)bis-(6-methyl-3-norbornyluracil) Wettable powder formulations willcontain from about 1,1-(1-oxoethylene) bis-(5,6-dimethyl-3-cyclohexyl-25 to 90 Weight percent poly uracil, from 0.5 to 2.0 weight uracil)percent wetting agent, from 0.25 to 5.0 weight percent 1 l dispersant,and from 9.25 to 74.25 weight percent inert extender, as these terms aredescribed above.

High-strength compositions generally consist of 90 to 99.5% poly uracil,and 0.5 to 10% of a liquid or soild surfactant such as those describedby McCutcheon in Detergents and Emulsifiers 1965 Annual. Suchhighstrength compositions can often be used in a manner similar to thewettable powders but they are also suitable for further formulation.

The organic liquid suspension concentrates are prepared by mixingtogether and sandgrinding a slurry of oilinsoluble active ingredient inthe presence of dispersing agents.

These organic liquid suspension concentrates will contain from 15 to 40%of the poly uracil, from 45 to 70% organic liquid such as kerosene,mineral oil and certain weed oils with the remainder made up ofsurfactants, corrosion inhibitors, and suspending agents.

Dusts are dense powder compositions Which are intended for applicationin dry form in accordance with the preferred compositions of theinvention. Dusts are characterized by their free-flowing and rapidsettling properties so that they are not readily windborne to areaswhere their presence is not desired. They contain primarily an activematerial and a dense, free-flowing, solid extender but may also containgrinding aids and surfactants.

Thus, the dust compositons will comprise about 5 to 20 weight percentpoly uracil, 5 to 50 weight percent absorptive clay filler, 0 to Weightpercent wetting agent, and about 30 to 90 Weight percent dense,free-flowing dust diluent, as these terms are used herein.

Emulsifiable oils are usually solutions of poly uracil in non-watermiscible solvents together with a surfactant.

For the compositions of this invention, emulsifiable oils can be made bymixing the poly uracil with a solvent and surfactant. Suitable solventsfor the compounds of this invention are aromatic hydrocarbons includingmany weed oils, chlorinated solvents, and non-water miscible ethers,esters, or .ketones.

Thus, emulsifiable oil compositions will consist of from about to 50weight percent poly uracil, about 40 to 82 weight percent solvent, andabout 1 to 10 Weight percent emulsifier, as these terms are defined andused above.

Granules and pellets are physically stable, particulate compositionscontaining a poly uracil which adheres to or is distributed through abasic matrix of a coherent, inert carrier with macroscopic dimensions.In order to aid leaching of the poly uracil from the granule or pellet,a surfactant can be present.

For the compositions of this invention, the inert carrier is preferablyof mineral origin, and the surfactant is a compound known to the art asa wetting agent.

There are two suitable types of carriers for the granule compositionscontaining compounds of the invention as an active material. The firstare porous, absorptive preformed granules, such as preformed andscreened granular attapulgite or heat expanded, gnanular, screenedvermiculite. On either of these, a suspension of the poly uracil can besprayed and can be absorbed at concentration up to 35 weight percent ofthe total weight. The second, which are also suitable for pellets, areinitially powdered kaolin clays, hydrated attapulgite, or bentoniteclays in the form of sodium, calcium or magnesium bentonites.Water-soluble salts, such as sodium salts, may also be present to aid inthe disintegration of granules or pellets in the presence of moisture.These ingredients are blended with the active components to givemixtures that are granulated or pelleted, followed by drying to yieldformulations with the active component distributed uniformly throughoutthe mass. Such granules and pellets can also be made with 25 to 30weight percent poly uracil, but more frequently a concentration of about10 weight percent is desired for optimum distribution. Granular 12compositions are most useful in a size range of 15 -30 mesh.

Thus, the prefered granular or pelleted formulations comprise about 5 to30 weight percent poly uracil, about 0 to 5 weight percent wettingagent, and about to weight percent inert mineral carrier, as these termsare used herein.

The compositions of this invention exert herbicidal activity on a broadspectrum of plants. They are useful as general purpose weed killers orsoil sterilants for control of vegetation on industrial sites andrailroad ballast particularly in areas of high rainfall.

These compositions also exhibit selective herbicidal action in crops. Byproperly selecting a bis-uracil of the invention and a rate and time ofapplication, weeds growing in such crops as blackberries, asparagus,sugar beets, mint, sisal, peaches, and sugar cane can be controlled.

The amount of bis-uracil herbicide to be used in any instance will begoverned by such factors as climate, the type of Weed to be controlled,soil conditions, and the like, and so it is not possible to give a rateof application suitable for all situations. Generally speaking, one usesthe bis-uracils at levels of 0.25 to 8 pounds per acre for selectivecontrol in crops. Rates of 5 to 40 pounds per acre are satisfactory forgeneral weed control.

The poly uracils of the invention uncouple in the presence of moist soiland therefore owe their herbicidal activity to the uracil herbicidecomponents. It is believed that the poly uracils are uncoupled byhydrolytic action in the moist soil or by microbial breakdown undernormal soil conditions capable of supporting weed growth, or both ofthese conditions.

The compositions of the invention therefore provide for the slow releaseof the active substituted uracils. Such compositions, which can bechemically tailored to release a highly active uracil at almost anydesired rate, can have far-reaching practical advantages over theconventional type of slow-release compositions which derive theirrelease properties from a purely physical condition or form.

The following examples better illustrate the manner in which thecompounds of this invention are formulated and used as herbicidalagents.

EXAMPLE 7 Percent I,1'-carbonylbis(5-bron1o 3 sec butyl-6-methyluracil)25.0 Attapulgite clay 69.5 Synthetic silica 2.0 Dioctyl sodiumsulfosuccinate 2.0 Sodium lignin sulfonate 1.5

The above ingredients are blended, micropulverized to a particle sizeessentially below 50 microns and then reblended.

The above material is suspended in water at the rate of 20 pounds ofactive ingredient per 50 gallons of suspension. This material is appliedpre-emergence to areas in a tank farm at rates of 50 to gallons peracre. The exact volume applied is predicated on the plant species to becontrolled and the duration of control desired. Such weeds as crabgrass(Digitaria spp.), barnyard grass (Echinochloa crusgalli), lambsquarter(Chenopodium album), dog fennel (Helenium tenuifolium'), Johnson grassseedlings (Sorghum halepense), bluegrass (Poa spp.), wild garlic (Alliumvineale), dock (Rumex spp.), peppergrass (Lepidium virginicum) andpoison ivy seedlings (Rhus radicans) are controlled for an extendedperiod.

All of the other compounds of the invention can be formulated andapplied in like manner.

EXAMPLE 8 Percent 1,1'-oxalylbis(5-bromo-3-sec-butyl-6-methyluracil)80.0 Montmorillonite clay 14.5

13 Synthetic silica 2.0 Sodium alkyl naphthalene sulfonate 3.0Methylated cellulose 0.5

The above ingredients are blended, micropulverized to a particle sizeessentially below 50 microns and then reblended.

The formulation is suspended in water to provide a ratio of 14 pounds ofactive ingredient in 50 gallons of water which is applied on one acre ofa grass rhizome barrier strip encircling citrus orchards. The chemicalis thoroughly incorporated by disking or rototilling to a depth of 8inches within 2 hours after application. Control of torpedo grass(Panicum repenu), Bermuda grass (Cynodon dactylon), Johnson grass(Sorhgum halepense), and Centipede grass (Eremochola ophiuroldes) isobtained. There is no injury to the citrus plants provided barrierstrips are no closer to trees than 50 feet.

The following compounds can be formulated and applied in like manner:

1.1-oxalyl bis (3-isopropyl-5-bromo-6-methyluracil) 1,1-oxalyl bis(3-tert-butyl-5-chloro-6-methyluracil) 1,1-oxa1yl bis[3-cyclohexyl-6,7-dihydro-5-cyclopenta(d) pyrimidine-2,4-(1H,3H)-dione]1,1-malonyl bis (3-sec-butyl-5-bromo-6-methyluracil) 1,1-terephthalylbis (3-sec-butyl-5-bromo-6-m thyluraci1) 1,1 perhydroterephthalyl bis(3-sec-butyl-5-brorno-6- rmethyluracil) 1,1-oxalyl bis(3-tert-butyl-5-bromo-6-methyluracil) EXAMPLE 9 PercentB-tert-butyl-S-chloro-1-( -bromo-3-tert-butyl-1,2,3,4-

tetra'hydro-6-methyl-2,4-dioxo-l-pyrimidinyl carbonyl)-6-methyluracil 25Kaolinite 69 Calcium sulfate dihydrate 2 Nonyl phenyl polyethyleneglycol ether 3 Sodium lignin sulfonate 1 The above ingredients areblended, rnicropulverized to a particle size essentially below 50microns and then reblended.

A 25% wettable powder formulation is suspended in water and applied witha tractor mounted sprayer so that 2 to 4 lbs. of active ingredient isapplied on one acre of asparagus in the spring before the spears emerge.Good control of lambs quarters (Chenopoa'ium album), ragweed (Ambrosiaantemisifolia), mustard (Brassica nigra), chickweed (Stellaria media),crabgrass (Digitaria spp.) and goosegrass (Eleusine indica) is obtainedthrough the cutting season. No crop injury is experienced.

The following compounds can be formulated and applied in like manner:1,1-(1-oxoethylene) bis (5-bromo-3-sec-butyl-6-methyluracil) 1,1'-(1-oxo-2-methylethylene) bis-(5-chloro-3-tert butyl- 6-methyluracil)EXAMPLE 10 Percent 1,1'-oxalyl'bis(3-tert-butyl-5-chloro=6-methyluraci15.0 Calcium lignin sulfonate plus wood sugars 9.7 Dioctyl sodiumsulfosuccinate 0.3 -30 mesh attapulgite 85.0

The active material, the calcium lignin sulfonate plus wood sugars andthe wetting agent are micropulverized to a particle size substantiallyless than 100 microns. This product is suspended in water and sprayed onthe granules of attapulgite which are tumbled in a mixer. Followingdrying, the granules are ready for application.

Twenty pounds of the above granular formulation (equivalent to 4lb./acre of active ingredient) are spread on an acre of Louisiana sugarcane in the spring just after off baring. Good control of crabgrass(Digitaria spp.),

14 barnyard grass (Echinochloa crusgalli), mustard (Brassica spp.),chickweed (Stellaria media), lambsquarter (Chenopodium album), andJohnson grass (Sorghum halepense) seedlings is obtained with nosignificant injury to the crop.

EXAMPLE 11 Percent 1,1'-phthalylbis[3-phenyl-5,6,7,8-tetrahydro-2,4-(1H,

3H)-quinazo-linedione] 10 Diatomaceous silica 5 Micaceous talc 85 Theabove dust is prepared by blending and grinding the active material withthe minor diluent, then blending the resulting powder with the majordiluent.

The above dust formulation is applied with a dust blower to generalweedy vegetation around the swampy edge of a pond so that 20 lbs. ofactive ingredient are applied on one acre. Good control of general weedspecies is obtained permitting a freer flow of water, and thus reducingareas of impounded water that provide breeding grounds for mosquitos.

EXAMPLE 12 Percent 1,1'-oxalylbis(5-bromo-3-tert-butyl-6-methyluracil)10 Sodium sulfate, anhydrous 10 Calcium lignin sulfonate 5 Kaolinite 75The above components are ground to pass a 50 mesh sreen, moistened withwater and extruded and cut to form pellets approximately x in size. Thepellets are dried and can be used as such or can be further subdividedinto granules in the 15-60 mesh range.

The above pellets or granules are applied with an auger spreader onrailroad rights of way so that 20 lbs. of active ingredient are appliedon one acre of actually treated area. Good control of foxtail (Satariaspp.), broomsedge (Andropogon virginicus), Bermuda grass (Cynodondactylon), and marestail (Erigeron canadensis) is obtained.

EXAMPLE 13 Percent 1,1-sebacylbis(3-sec-butyl-5-brorno-6-methyluracil)15 Alkylaryl polyethylene glycol ether 5 Isophorone The aboveemulsifiable oil is prepared by mixing the components with agitationuntil a homogeneous solution results. The oil may be emulsified withwater or extended with weed oil for application.

EXAMPLE 14 Percent 1,1 carbonylbis(5 bromo 3 tert butyl-6-methyluracial)25 Sodium lauryl sulfate 35 Sodium lignin sulfonate 2 Attapulgite clay35 Synthetic silica 3 The above components are blended, micropulverizedto a particle size below 50 microns and reblended.

A mixture is made with water using the formulation mentioned above toprovide a concentrate of 8 lbs. of active ingredient in 50 gal. ofcarrier and is sprayed on one acre of blackberries. The spray mixture isdirected toward the base of the plant on to freshly cultivate soil justprior to the time new leaves emerge in the canes in the spring. A repeatapplication of 4 lbs. per acre one month later provides full season weedcontrol. Good control of chickweed (Stellaria media), henbit (Lamiumamplexicaule), lambsquarter (Chenopodium album), field cress (Rorippaaustriaca), wild mustard (Brassica spp.), crabgrass (Digitaria spp.) andgoosegrass (Eleusine indica) is obtained.

EXAMPLE 15 Percent 1,1'-carbonylbis(3-sec-butyl-5-chloro-6-ethyluracil)30 Soya lecithin 2 Mineral oil 63 Sorbitan hexaoleate 5 The above oilsuspension is prepared by first grinding the active compound to pass a40 mesh screen. All the components are then mixed and sand ground to aparticle size substantially below 5 microns. The product ischaracterized by its extermely small particles size so that when dilutedwith weed oil or emulsified in water and sprayed, plant foliage isuniformly coated.

The above formulation is suspended in herbicidal oil to form aconcentrated homogeneous suspension. The suspension containing lbs. ofactive ingredients in 30 gallons of carrier is applied by high pressuresprayer mounted on a helicopter and distributed over one acre of areafor fire-break maintenance. Good control of crabgrass (Digitaria spp.),foxtail (Setaria spp.), broomsedge (Andropogon virginicus), maple (Acerspp.) sprouts and mountain laurel (Kalmia latifolia) sprouts isobtained.

EXAMPLE 16 Percent 1,1 carbonylbis (5 bromo 3 sec-butyl-6-methyluracil)97 Alkylaryl polyethylene glycol ether 3 The above components areblended and ground to pass a 20 mesh screen. This composition issuitable for further formulation or under some circumstances can be useddirectly as a granular material.

Without further alteration, this formulation is spread by hand or with afertilizer spreader capable of distributing granules uniformly. Twopounds of the partially granulated mixture is spread evenly over 1,000square feet of crushed rock, sand, gravel or ballast before applying anasphalt road surface. Good control of Bermuda grass (Cynodon doctylon),Johnson grass (Sorghum halepense) and torpedo grass (Panicum repens) isWhat is claimed is:

1. A compound of the formula:

wherein:

R is selected from the group consisting of alkyl of 3 through 28 carbonatoms, phenyl, 'benzyl, cycloalkyl of 5 through 8 carbon atoms, andsubstituted cycloalkyl of 5 through 8 carbon atoms wherein saidsubstituent is selected from the group consisting of methyl and methoxy;

R is alkyl of 1 through 3 carbon atoms;

X is selected from the group consisting of methyl, chlorine, bromine,and iodine with the proviso that X can be hydrogen when the R on thesame ring is a cycloalkyl group, and with the further proviso that X canbe joined with R to form a trimethylene or tetramethylene bridge; and

Z is selected from the group consisting of where:

R is hydrogen or alkyl of 1 through 4 carbon atoms and R is alkylene of1 through 12 carbon atoms, alkenylene of 1 through 12 carbon atoms,cyclohexylene, 0r phenylene. 2. A compound of claim 1 represented by theformula:

wherein R is selected from the group consisting of alkyl of 3 through 8carbon atoms, phenyl, benzyl, cycloalkyl of 5 through 8 carbon atoms,and substituted cycloalkyl of 5 through 8 carbon atoms wherein saidsubstituent is selected from the group consisting of methyl and methoxy;R is alkyl of 1 through 3 carbon atoms; and X is selected from the groupconsisting of methyl, chlorine, bromine, and iodine, with the provisothat X can be hydrogen when the R on the same ring is a cycloalkylgroup, and with the further proviso that X can be joined with R when Xis methyl to form a trimethylene or tetramethylene group. 3. Thecompound of claim 1 which is 1,1-oxalylbis(5-bromo-3-sec-butyl-6-methyluracil.

4. The compound of claim 1 which is 1,1'-oxalylbis(5-bromo-3-tert-butyl-6-methyluracil) 5. The compound of claim 1 which isl,l'-oxalylbis[5- bromo-3 3-pentyl -6-methyluracil] 6. The compound ofclaim 1 which is 1,l'-oxalylbis(3- se'c-butyl-S -chloro-6-methyluracil)7. The compound of claim 1 which is 1,l'-oxalylbis(3-tert-butyl-S-chloro-6-methyluracil) 8. The compound of claim 1 which is1,1'-carbonylbis (5-bromo-3-sec-butyl-6-methyluracil) 9. The compound ofclaim 1 which is 1,1'-carbonylbis (5 bromo-3-tert-butyl-6-rnethyluracil) 10. The compound of claim 1. which is1,1-malonylbis (5-bromo-3 -sec-butyl-6-methy1uracil) References CitedUNITED STATES PATENTS 3,471,282 10/ 1969 Kugele 71-92 2,987,514 6/ 1961Hughes et al 71-92 2,987,515 6/ 1961 Stromberg et a1. 71-92 2,987,521 6/1961 Hughes et a1 71-92 3,138,596 6/1964 Kloastermon 260-260 3,235,3602/1966 Soboszenski 71-92 3,235,363 2/1966 Luckenbaugh et al 71-923,301,654 1/ 1967 Dalton 71-92 OTHER REFERENCES Feldman, FormaldehydeCondensation of 6-aminouracils, (1961) CA. 56, pp. 1736-37 (1962).

Bredereck et al., Catalytic Action of Tetraalkylureas etc., 1965 CA. 62,p. 11807 (1965).

Novacek et al., Acylation of 6-Azauracil etc., (1965) CA. 63, pp.l3382-83.

Thehara et al., Polynocleotides, etc., (1965) C.A. 63, p. 13381.

JAMES O. THOMAS, 1a., Primary Examiner US. Cl. X.R. 71-92 UNITED STATESPATENT OFFICE CERTIFICATE OF CQRRECTION Patent No, 3,532,699 DatedOCtObT 6, 197:)

Inventor(s) Thomas G Kugele It is certified that error appears in theabove-identified patent and that said Letters Patent are herebycorrected as shown below:

In Claim 1 at line 62 "28" should read 8 Signed and sealed this 16th dayof March 1971 (SEAL) Attest:

EDWARD M.FLETCHER,JR. WILLIAM E. SCHUYLER, JR. Attesting OfficerCommissioner of Patents FORM PO-1050[\O69) uscoMM Dc 603764269 u.seovuuuzln' unmarorncz: nu o-an-au

